Triethylamine → 2-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid

HRID 249623Notes

Reaction equation

HRID 249623 reaction equation
[CH:1]1[C:6](N=C=S)=[CH:5][C:4]2[C:10]([O:12][C:13]3([C:23]4[CH:24]=[CH:25][C:26]([OH:28])=[CH:27][C:22]=4[O:21][C:15]4[CH:16]=[C:17]([OH:20])[CH:18]=[CH:19][C:14]3=4)[C:3]=2[CH:2]=1)=[O:11].CCN(CC)CC>CN(C=O)C.C(Cl)Cl>[CH:1]1[CH:6]=[CH:5][C:4]([C:10]([OH:12])=[O:11])=[C:3]([C:13]2[C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=3[O:21][C:22]3[C:23]=2[CH:24]=[CH:25][C:26]([CH:27]=3)=[O:28])[CH:2]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 18730Fluorescein 5-isothiocyanate

Product 1

HCID 33832-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acidYield 386.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The starting amine (5) (0.15 g, 0.12 mmol) and fluorescein isothiocyanate (FLITC) (0.056 g, 0.14 mmol) were dissolved in a mixture of DMF and CH2Cl2 (6 mL, 1:5 ratio) at room temperature. The reaction was cooled to 0° C., and then an excess amount of Et3N (66 μL, 0.48 mmol) was added dropwise. An orange colored precipitate was immediately formed and remained during the entire period of the reaction. After completion of the reaction, the insoluble precipitate was filtered off; and the solvent was removed under reduced pressure. The residue was diluted with CH2Cl2 (15 mL), washed with 1N HCl (2×15 mL) and H2O (2×15 mL). The organic phase was dried over anhydrous Na2SO4 and evaporated under reduced pressure to afford 0.18 g (92%) of fluorescein-labeled guanidine (17) as an orange colored foam-shaped solid. 1H NMR (CD3OD): δ 8.20 (s, 1H, ArH), 7.86 (m, 1H, ArH), 7.22 (m, 2H, ArH), 6.64 (m, 3H, ArH), 6.56 (m, 2H, ArH), 3.86 (m, 2H, CH2NHCS), 3.66 (m, 12H, CH2O), 3.46 (m, 6H, CH2NHCO), 3.38 (m, 6H, CH2NH), 2.58 (m, 2H, CH2CO), 2.42 (m, 6H, CH2CO), 1.48 (s, 27H, t-Bu), 1.46 (s, 27H, t-Bu).

Workup

  1. customAn orange colored precipitate was immediately formed
  2. customremained during the entire period of the reaction
  3. customAfter completion of the reaction
  4. filtrationthe insoluble precipitate was filtered off
  5. customand the solvent was removed under reduced pressure
  6. additionThe residue was diluted with CH2Cl2 (15 mL)
  7. washwashed with 1N HCl (2×15 mL) and H2O (2×15 mL)
  8. dry with materialThe organic phase was dried over anhydrous Na2SO4
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-96de8f913c1b408aa30a6a788462db75
Source dataset
uspto-grants-2011_01
Patent number
US07862807B2

Reaction notes

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